For Your Eyes Only
by Destielcaptain
Summary: Set on the island of Manhattan, the characters of Gossip Girl and Supernatural go to school at Constance and St. Jude's, where they will face tribulations of romance, betrayal, and unknown forces that threaten the lives and reputations of our favorite elites. characters/pairings: Destiel; Megstiel; Samicca; Ruby/Sam; Blair; Chuck; Nate; Dan; Jenny; Vanessa; Ash; Kevin Tran; Jo
1. Prologue - The First Blast of Fall

_Hey there Upper-East siders. Gossip Girl here. Your one and only source into the scandalous lives of Manhattan's elite. Today is rather a special occasion. Why, you ask? Because this is my first post of the Fall. That's right, it's a new school year at Constance Billard and St. Jude's, and a new year full of drama, scandals, and gossip, and I'll be here to whisper all the juicy secrets._

_Let's have a re-cap of our favorite Manhattan-dwellers, shall we? First on my hit list, Serena van der Woodsen, everyone's favorite it girl, along with her slightly-less-noteworthy brother Eric, has returned from a sun-soaking stay at the Hamptons. Newly single since her split with lonely boy, all the guys at St. Jude's will be standing in line to take her and her international smile out to Butter and a movie. Every guy except her brother's boyfriend, that is. Rumor has it that E has a new man named Jonathan, and he's quite the hunk. Dry your eyes ladies, Chuck Bass is now available after Blair Waldorf left him for her Prince Charming. Literally. Lord Marcus Beaton whisked B away on a romantic summer getaway in the finest locations of England. Apparently they're still going strong. We'll see how long that lasts. Knowing B, she'll dump him at the first red flag. Poor Bass seems pretty down about it. If you ever wanted to console him, now's your chance ladies. _

_Meg Masters has exchanged her blonde bangs in for a dirty brunette do. I guess she took the break up with Crowley real hard. She could always ask out Charlie Bradbury. If anyone could find her. Apparently she couldn't take all the lesbian rumors about her and Dorothy Baum and high-tailed it to Kansas. Dorothy is still back however, bud don't bring up Charlie around her, or she might tear you a new one._

_In other news, Nate Archibald is supposedly single, but due to recent evidence sent in by a loyal friend I have reason to believe he is in a secret relationship. Why the anonymity Nate? Living in the Upper East Side, where anything can happen, I for one would not be surprised if it turned out to be his bestie Chuck Bass. They always seemed particularly close._

_Gordon Walker is back in rehab. For the third time. It doesn't seem his parents will let him out this time, so the Upper East Side might have to say its final goodbyes to its #1 pot dealer. _

_I'm surprised I'm even mentioning him, but our lonely boy, Dan Humphrey, had a particularly not-so-lonely summer. Probably just rebounding from Serena, the one that got away. Speaking of things getting away from lonely boy, I hear he got fired from his summer internship after a mere few weeks. Cheer up lonely boy. If the writer thing doesn't work out, Blair's mom Eleanor is always looking for more cater waiters to work her fashion shows. _

_Speaking of Eleanor, lonely boy's little sis Jenny is currently doing an internship with Waldorf designs, however knowing B, lil' J won't make it to the end of the month. Her Brooklyn bestie Vanessa Abrams is left broken hearted after giving her heart to Nate, only to have it thrown right back in her face. Don't worry though, they're still friends. _

_Castiel Milton, still rocking the adorable messy black hair and khaki trench-coat, returns from a summer studying abroad. That's right darlings, after three years at St. Jude's he remains the one to beat for the spot of valedictorian. After the reigns of his older brothers, little Cas filled in a large pair of shoes nicely. His little sister Anna remains the red-hot shining star of the Constance junior class, still sporting her signature cherry red hair and good-girl image. _

_I also couldn't help but notice that Sam Winchester is still dating Ruby Pellegrino. Looks like he believes her about her not cheating on him with his friend Ash. Hasn't little Sammy learned that only humans deserve second chances, and not demons? I speak metaphorically, of course. _

_Jessica Moore, though appearing confident and strong for the cameras I have my minions keep on her, does not seem to be over little Sammy. I wonder how she feels being so deep into his friend zone that he stays with his cheating GF instead of taking her up on the offer she gave him last Spring that left her standing alone at Madison Square Park._

_Georgina Sparks? Nowhere to be seen. Guess it goes to show: if Blair Waldorf wants you out of Manhattan, you will leave Manhattan. To this day, not even Gossip Girl knows where she is. B really knows how to perform a banishment. _

_Jo Harvelle remains the poster-child for tough girls at Constance Billard. Still having never had a BF, she is a single lady who don't need no man. Better bring home the gold in this years lacrosse tournament Jo. _

_Last but not least on my hot list: Dean Winchester, the new it boy now that Nate Archibald and Chuck Bass are either spoken for or tending to a broken heart. The attractive star quarterback of St. Jude's football team is every Manhattan girl's wet dream. Don't get your hopes up too high though ladies (and some gentlemen I'm sure), rumor has it that he has his eyes set on the newly single it girl, the one and only miss Serena van der Woodsen. An it couple as perfect as these two would be the perfect way to kick off another drama-filled school year. As well as a couple of pregnancy scares. _

_I can't wait to share the last year of high school for our it crowd with you darlings. I am nothing without you. _

_You know you love me,_

_XOXO_

_Gossip Girl. _


	2. Chapter 1 - Keep Your Friends Close

"Can you believe this? She paints me like some commitaphobe heartbreaker! That gossiping snake doesn't know the half of it!", Blair fumed, as she and her best friend Serena climbed the steps of Constance Billard School for Girls, the private school they had been attending since kindergarten, except for the year Serena went to boarding school, of which she rarely spoke.

"I know B," replied Serena, "but you have to remember that Gossip Girl rarely knows everything about a story before she posts about it. Otherwise I might not still look like the ditzy it girl that's only good for taking out on a date and then dumping the morning after."

"And she wouldn't be pairing you with the likes of Dean Winchester. Obviously whoever sent in _that _tip doesn't know that you have higher standards," Blair said smugly. "Honestly, I don't know why all the constance girls go nuts over him. Don't they know he's just Brooklyn trash?"

"Oh c'mon B, that is mean, even for you!", said Serena, obviously thinking about her own Brooklyn "trash" ex-boyfriend.

"Serena, did you learn nothing from the experience with Dan?", asked Blair. _How did she know I was thinking about him?!, _thought Serena.

"Because I can read your mind.", replied Blair with a big grin on her face, flipping her chestnut brown hair back. Serena continued to look stunned as they sat down on their desks in the calculus classroom. "Serena, we've only been best friends since kindergarten! I can usually tell what you're thinking."

"Oh really? Well what am I thinking about now?", asked Serena confidently.

"Well I'm not a psychic.", said Blair with a wink. Serena giggled. "But I hope it's not about Dean Winchester.", she said with a serious you-better-not tone in her voice.

"Blair, I already told you! Gossip Girl has it wrong. I do not have feelings for Dean Winchester. I've spoken to him maybe a few times all of high school!"

"Well he certainly feels otherwise", said a soft voice coming from the door of the classroom. The angelic Anna Milton graced the room with her strawberry-red hair and pale complexion.

"Oh Anna!", said Blair with a slightly-over-done falsified fondness, "so good to see you! I didn't know that you're taking senior calculus with us this year!"

"Yeah well I took trig over the summer while studying abroad with my brother Castiel, so I was able to skip ahead in mathematics!", said Anna brightly.

Nobody could deny that Anna was a doll. She was always cordial and respectful to everybody. On top of that, she was caring and friends with everyone at Constance and easily half of St. Jude's. If someone had a bad day, she was there to comfort them. If someone was struggling carrying something, she would help carry the load or hold a door open for them. If someone was failing a class, or close to failing, she would always be the first one to offer free tutoring. She was not a needy attention-whore who had to be liked by everybody. She was just genuinely a sweetheart, which only made her that much more adorable. It was unfortunate that some people, like Blair, would try to take advantage of her kind nature. Interestingly enough, however, Anna's child-like innocence did not come with child-like ignorance. She was in no way blind to people's flaws, and she most certainly would not let people walk over her. Ever since she was a fresh fish at the big pond that is Constance, Blair has had her pegged for an easy target and has tried with much effort to make her a minion. However, Anna knows better than to subject herself to the same torment under which Blair puts her "friends".

Serena knows that Blair is a manipulator, but she seems to be the only student at Constance or St. Jude's save a few others that can pierce her tough outer shell and see that inside she was a somewhat genuinely caring person who would do anything for the people she loves. That was probably Serena's most admirable quality; she did not give up on people in which she believed. Besides Georgina Sparks, this never failed to produce a positive result.

It's unfortunate that so many people are unable to actually see how great of a person Serena is. You don't become Manhattan's "it girl" by being intelligent or funny. The only things anyone seems to notice about Serena are her golden blonde hair, her flawless tan skin, her long beautiful legs, her winning polar-white smile, her rich hazel-blue eyes, and her perfectly proportioned breasts.

All of these thoughts went through Serena's mind as Blair and Anna talked about their summers ("and in Germany we studied theoretical physics, and in Italy we studied…" "Lord Marcus took me to see the most beautiful places in England. Have you ever been to the Exbury Gardens?") and then the words that chiming voice had spoken when its owner walked into the room rang in Serena's ears, making her jump.

"Wait a minute! What did you say?!", Serena practically shouted, making the whole classroom jump with a stutter, then gradually go back to what they were doing.

"I was just telling Blair how wonderful her trip sounded…"

"No! Earlier, when you walked into the room, you said that Dean Winchester feels otherwise when I said I didn't have feelings for him.", Serena interjected impatiently, not really caring about Blair's trip because let's face it, she had heard it a million times already.

"Oh yeah!", said Anna with a sudden glimmer in her eye. "He really likes you.", she smiled.

"Wait, what?", Serena pondered. How could a guy whom she barely knows have feelings for her? They had spoken… what, maybe five times since they began high school?

"It's quite alright Serena, you have my blessing. I think you two would make a great couple.", Anna said brightly. She and Dean had dated fairly seriously two years ago. Fairly seriously for Dean Winchester that is, meaning they lasted a whole school year and two weeks into the next summer before Anna decided he wasn't mature enough for her.

"Oh no, Anna… I mean thank you, but that's not what I meant…"

Anna cut her off. "Serena, whatever you want to do, I support it. Be with him, don't be with him, I'm good either way." Anna smiled at her so warmly that Serena couldn't help but admire her even more. Only someone like Anna would be totally okay with something like this. According to the rules of girl world, ex-boyfriends of girlfriends were off limits. But Anna plays by her own set of rules.

"I appreciate it, really Anna I do! But it's moot because I don't like him anyways," Serena declined politely.

"Yeah, Serena could do so much better.", interjected Blair.

Anna gave her a judgmental face. While they are no longer an item, she and Dean were still good friends, and Anna doesn't like it when people insult her friends. "What exactly do you mean Blair?", she asked poignantly.

"Oh here we go…" said Serena.

They argued for a few minutes before a beeping sound filled the room and everyone got their phones out. A Gossip Girl blast.

_Spotted._

_Dean Winchester getting friendly with one Bela Talbot right before classes start. Be careful Dean-o, I hear kitty likes to scratchy. _

_XOXO,_

_Gossip Girl._

"I'm going to have to have a talk with that boy.", Anna sighed.

Serena just laughed. She may not have known much about Dean Winchester, but if there was one thing she did know, it was that he went through girls faster than Blair went through boys, which is really saying something. "He is such a player," Serena mused.

"And that's just how you like them," Blair teased with a shit-eating grin on her face.

"I thought you didn't approve?" Serena stuck her tongue out, quickly pulling it back upon realizing how childish her actions were, while Blair and Anna laughed.

"Hey, if I get to make fun of you, I'm okay with you dating whomever you want.", Blair said with a wink.

Serena laughed while internally questioning her choices in friends as the Constance school bell rang, signaling the first day of senior year.

"Alright class, take your seats," said Frank Devereaux, the calculus instructor at Constance and St. Jude's. "As this is the first day of the school year, I'm going to start you off with some review of the concepts you learned in trigonometry and algebra 2…"

And he was off. Professor Devereaux lived up to his reputation; he was all about getting through with the task at hand, and had no time for tomfoolery, as Serena and Blair would learn within the first ten minutes of the day.

"Ms. Waldorf and Ms. van der Woodsen, what is so important that it takes priority over my class?!", he demanded as Blair and Serena's hushed whispers immediately halted and all eyes in the classroom were focused on them.

"Oh, um…", Serena trailed off and looked to Blair for help desperately.

But before Blair had a chance to speak, Anna interjected. "They were discussing how the square root function is the inverse of the quadratic function. Serena was asking Blair for confirmation of this fact and Blair was explaining why she was correct. That was all." Anna gave the warmest smile ever. Not even straight-shooter Professor Devereaux could resist. He congratulated Serena on the observation and commended Blair for her knowledge of the topic and resumed teaching, while Serena and Blair resumed whispering about boys.

"He probably doesn't even like me. Gossip Girl was most likely just messing with me. Earlier today she says he like me, and then an hour later he is making out with Bela Talbot? I'm betting it was just false information sent in by someone wanting to screw with the it girl," Serena whispered.

"Or screw _on _the it girl," Blair whispered back slyly with a smirk on her fox-like face.

"What are you getting at?", asked Serena.

"I'm saying maybe Dean Winchester sent that tip in himself because he likes you and wants to hit that," Blair responded, gesturing to Serena's ass.

"Blair that is so gross!" Serena whispered/yelled back while Blair laughed smugly.

"Alright girls, I appreciate it that you're so interested in what I am teaching, but let's put a stop to the whispering, okay? I wouldn't want to have to separate a pair of best friends," said Professor Devereaux.

"Yes sir," Serena respectfully replied.

"Sure thing Frank," responded Blair casually while all the other girls in the room gasped in horror. No one ever talks to a professor like that at Constance. Especially not Frank Devereaux.

"Blair, what is the matter with you?!", Serena asked, genuinely concerned for her best friend's well-being. This was in no way like Blair Waldorf. She was always respectful to her elders. Made it easier to manipulate them. But ever since the beginning of the school year, hell even before that, Serena noticed that Blair had been acting way out of her element. Ever since the Hamptons. Ever since… ever since she met _him_.

And suddenly Serena figured out why Blair had been acting so off lately. She made a mental note to talk to her about it later, if Professor Devereaux didn't kill her first. And if looks could kill, Blair would be sitting dead at her desk because the one Frank was giving her could scare anyone to the brink of a heart attack.


	3. Chapter 2 - And Your Enemies Closer

"So you're really serious about this girl?", Sam asked.

"Yup," Dean responded with seeming indifference.

"Wow."

"What?"

"Nothing! I'm just surprised, that's all. Dean Winchester, taking a relationship seriously."

"Why is that surprising?"

"Well, not to bring up negative things from the past Dean, but you haven't taken a relationship seriously since Anna."

And Sam wasn't wrong. Dean just hated to admit it. He had something so great, and he threw it all away over something that would become meaningless after high school.

"Well Serena seems cool. And she's hot."

"And unattainable I hear."

"Challenged accepted," said Dean with a wink while Sam rolled his eyes.

The Winchester brothers gathered their things and headed out the door of their Brooklyn loft, saying goodbye to no one, as their father was at work (typical Monday morning) and their mother died in a house fire when Sam was still at breastfeeding age. They walked up to Dean's chevy impala, or as Dean called it, "baby". It wasn't like the other cars of students at Constance and St. Jude's. Most of them were brand new shiny Volvos or Ferraris owned by rich kids living on the Upper East Side. But Dean liked his old car. "It has personality", he always said, and he wasn't wrong. The expensive cars the rich Upper East Side kids drove didn't have the plastic army soldier toy Sam stuck in the air vents when he was five that made a rattling noise every time Dean turned on the car in the winter. Nor did they have Sam and Dean's initials carved in the leather of the back seats that Sam and Dean did when they were eight and twelve. Having moved around a lot until he got scholarships to St. Jude's in High School, the impala always gave Dean a sense of home.

"Dude, you do realize that every guy at St. Jude's will have an eye on her, right?", Sam said to his brother.

"Yeah, well that's one thing you innocent little sophomores don't understand Sammy," Dean said with a chuckle when he called Sam by the nickname he had hated since he got to high school and wanted to become a mature adult (which did not entail being called "Sammy"), "the whole point about relationships being a battlefield is that you fight. You don't throw in the towel just because you've got some competition," Dean informed his little brother.

Sam just rolled his eyes at Dean as the two hopped into the impala and Dean revved up the engine, and the toy soldier rattled in the air vents, making both of the brothers smile. It was the perfect way to start the day, the Winchester way.

The drive was quiet for a little bit until Sam brought back up the topic of Serena.

"What are you even going to say to her? How are you going to ask?"

"I'm just gonna walk up to her, tell her I think she's cool, and ask to take her out."

"And what makes you so sure that's gonna work?

"Because I'm Dean motherfucking Winchester," Dean said only half-jokingly.

Sam rolled his eyes. Humility was not an attribute for which Dean was well-known. Sam often wondered how Dean managed to get girls so easily. He had the looks part down; Dean's adorable face, muscular build, perfectly cut dirty blonde hair, bad boy vibe, and smile to die for rarely failed to get him a date, but Sam often wondered why after said date the girl didn't run away and never look back. Sam cared about his brother more than anything in the world, but he was well aware that he could sometimes be a complete and total jackass to women. It was a miracle that Anna stayed with him for as long as she did, and managed to remain friends with him afterward, which were also notions that Sam pondered from time to time.

Sam worried for Serena. He is friends with her brother Eric, so he knows her fairly well and talks to her from time to time, and she's the kind of girl that Dean takes one look at and wants to hump and dump the next day, as he had done to many girls since his nasty break-up with Anna. Most brothers would be mad at, and maybe even a little jealous of their brother if they were like Dean Winchester. Sam on the other hand, being the caring and loving little brother that he is, worried for his brother. He has been for a long time, ever since Dean began his series of rendezvous'. Out of his sense of duty to his friend, he decided now was as good a time as any to speak up.

"Dean I'm worried about you," said Sam with a ripple of nervousness in his tone.

Dean looked at him curiously and gave a light laugh. "Why?", he asked, "What makes you say that Sam?"

"Dean, I don't know if you've noticed, but everyone else at Constance and St. Jude's has, including myself, so I'm going to address the elephant in the car," said Sam.

"Okay, shoot," said Dean, curiosity aroused.

Not exactly knowing how to begin, Sam decided it would be just best to rip the band-aid off quickly and get it over with. "You haven't had a relationship that you cared about since Anna, and ever since you two broke up you've turned into this womanizing one-night standing… man-whore, for lack of a better word. It's not healthy. And it's not just with women either; you rarely even speak to Dad anymore or Uncle Bobby, and even with me you've been distant."

Dean's facial expression shifted from being angry to uncomfortable to serious to hurt. "Why do you bring this up all of a sudden? I mean now? After two whole years, you never brought this up before."

"Because I didn't make the connection until recently, and then I struggled with finding the right circumstances to bring this up in."

"Well I don't know what you're talking about. I mean sure I've had my fair share of girls, but that doesn't make me a… what did you say, man-whore? It's normal for a teenage guy to do stuff. You should know, I gave you the talk when your penis started growing, right?", Dean nudged his little brother uncomfortably.

"It's more than just hormones Dean. It would take more than the ten fingers I have to count how many girls you've slept with in the last two years. Having urges is normal for teenagers, but acting upon those urges as much as you have are signs of serious emotional or mental afflictions."

"Well excuse me Dr. fucking Phil, but when did you get a PhD in psychology? I'm over Anna. Were friends now. There's no hard feelings."

"Yeah, but…"

"No 'buts' Sam! There is nothing left to say now! This conversation is over!", said Dean in a most firm tone of voice that made Sam shut up for the rest of the car ride.

As they pulled up to St. Jude's School for Boys Dean found a spot away from the rich kids so that they wouldn't make fun of him and his "junker car". Normally Dean would love to pick a fight, but due to frequent visits with the principle last year regarding fights into which Dean got because of kids taunting him, he decided it would be best just to leave the issue alone. The Winchester brothers got out of the impala and started their walk up to the building, adjacent to Constance Billard School for Girls, a fact which Dean loved, for obvious reasons.

Dean and Sam were about to part ways to their different classes when Ruby Pellegrino appeared out of nowhere like a supernatural entity (as she often seemed to do) and gave Sam a kiss on the cheek.

"Hey babe!", she said to Sam all sweet-like. "Hey Dean," she said with noticeably less enthusiasm.

"Hellion," Dean sneered.

"Hey!", said Sam, "that's my girlfriend, Dean!"

"Wow Dean-o, I at least tried to be cordial," said Ruby, kind of laughing because in all honesty, she couldn't give less shits when it came to Dean's opinion of her.

Dean got even more annoyed. He hated the name "Dean-o" that Gossip Girl gave him at the beginning of Freshman year.

"Yeah, well it's hard for me to be cordial to sluts who cheat on my brother," Dean taunted.

Now Sam was really angry. "Dean! Apologize! NOW!", Sam shouted.

"Babe, don't make a scene. I don't want to be on the sticky end of another Gossip Girl blast," Ruby said.

But Dean most certainly didn't give a shit about Gossip Girl. He loves to taunt her by causing scenes because he doesn't take her seriously.

"What's the matter Ruby?", Dean shouted, attracting the attention of everyone in the hallway, "You don't like it when people call you a tramp? Maybe you should've thought of that before you cheated on Sam with Ash."

"This again…," muttered Sam. The camera phones were already flashing.

"Dean," Ruby said with a feigned calm voice, obviously trying to contain serious rage and not cause a scene, "even if that had happened, now is _not _the time _nor _the place to talk about it."

"Whatever," Dean muttered as he walked away. He had gotten what he wanted. He figured that if he eventually put enough pressure on Ruby, she would crack, and Sam would finally see her for the cheating harlot Dean _knew _she was.

The bell wouldn't ring for another few minutes; Dean had just enough time to take a smoke break. He went behind a building and lit up a cigarette when Bela Talbot walked up to him. Dean immediately put his cigarette out and went to leave, but Bela, being the strong woman that she is, pinned him to a wall and planted a long wet one on him, leaving Dean out of breath and wide-eyed.

She merely laughed and said with her sexy British accent, "Wow Dean I didn't think you would've got so soft since our little rendezvous two summers ago."

She leaned in for some more, but very rarely a moment will come when Dean's rationality manages to overcome his "teenage boy desires". After their night together the summer before last, she would not leave him alone. She would often come to his house unannounced and called him on a thrice-hourly basis. Though she was undeniably hot, with her wavy brunette hair, captivating charisma, and killer figure, even Dean knew that she was certifiably insane.

"Not going there again Belly, sorry," Dean said matter-of-factly.

Bela shrugged and walked away, which Dean thought was strange. Why would she full-on spontaneously make out with him and then just walk away?

Dean was about to head to class, as the bell would be ringing any second, but then he heard a rustling bush and a pair of footsteps quickly pacing away around a nearby wall. Dean ran around it, hoping to catch who was no doubt one of Gossip Girl's minions, but like a ghost, they vanished without a trace.

Dean swore under his breath and made his way to class. The bell rang right as he entered his first period AP U.S. History classroom. The second he entered the room, glances were made at him and people were talking in hushed whispers, inevitably regarding the Gossip Girl blast. Dean didn't care about that though. As he once said to Sam, "The only people who care about what Gossip Girl says are little shits who have boring lives, so they have to find excitement in the drama of other peoples' lives."

"Hey Dean, I hear Kitty likes to scratchy," Kevin Chan teased.

"Blow me Kev," Dean wittily retorted.

"Hmm… no thanks. You're not exactly my type.", Kevin replied with a wink.

Dean laughed. Kevin Chan has been one of his best friends since the beginning of sophomore year. At the beginning of High school, Dean bullied Kevin because he was smart and Dean was jealous because at the time his grades were in the shitter. But Kevin, being the compassionate, understanding guy that he is, offered Dean his help in getting his grades up. During their study sessions together they bonded over surprisingly mutual interests, and now Dean would take a bullet for the guy.

"So… Bela Talbot, huh? Thought she was so two summers ago?"

"Hey it's not what Gossip Girl makes it look like," Dean replied with a hint of disgust when he said Gossip Girl's name, "she ambushed me."

"HA! A girl ambushed Dean Winchester? There's an interesting plot twist."

Dean rolled his eyes.

"Did you see the person that took the picture?", Kevin asked.

"Not a glimpse," Dean said with curiosity, which was surprising given that he acts apathetic to all things Gossip Girl, "it's like they just vanished into thin air…"

"…wait, you mean like literally vanished? Or, they were just really fast, or…?"

"Gee calm down Kev, I meant it figuratively. There are no ghosts running wild among St. Jude's," Dean said, taken aback by Kevin's sudden nervousness at the mention of ghosts.

Kevin still didn't look convinced. As a matter of fact, he looked legitimately _scared_. Before Dean could have a chance to ask him what was going on, Castiel walked into the classroom.

"Can I talk to you Dean?", Castiel asked.

"Yeah sure Cas, what's up?", Dean responded.

Castiel has been Dean's one true best friend since Dean moved to Manhattan at the beginning of High School. Unlike most Upper East Siders, Castiel was not materialistic, egocentric, and arrogant, but rather a loving, caring, intelligent individual. These qualities all attracted Dean to Castiel.

Castiel was a nerd, but that does not mean that he isn't easy on the eyes. His messy black hair made you just wanna run your hands through it while he was fucking you with his toned body, and his mesmerizing ocean-blue eyes could put you in a trance. The only thing that separated him from the other good-looking guys in his grade regarding his good genes was his humble attitude towards them, something about which Dean had consistently tried to do something. "You're a regulation hottie Cas. Own it," Dean always said to him. But Castiel wasn't like that. He didn't care that he had good looks, because he had no intention of using them for anything as his personality was very asexual. Not to say he was literally not interested in sex, but he always said that school was his top priority. This was surprising to no one, seeing as he came from the Milton family, all the boys of which had graduated St. Jude's valedictorian of their senior class and gone to ivy league colleges and had happy lives with successful careers afterward. The pressure on the Milton boys (and Anna too now that she is in high school) was notoriously massive.

"What did you want to talk about Cas?" Dean asked.

Castiel was about to speak up, but before he could begin, the bell rang and Rachel Carr walked into the room and said, "Alright class, time to begin the school year. For those of you who do not know me, which is probably all of you seeing as I'm a new teacher this year, my name is Ms. Carr. I will be teaching English to you seniors at St. Jude's and the girls at Constance as well. Let us begin, shall we? I'm assuming you all read Othello over the summer as you were supposed to…"

She trailed off and Dean scribbled a note to Cas that said _What is it?_, and Cas wrote one back saying _We'll talk later. _Dean looked puzzled for a second and then shrugged it off. Obviously if Cas said it could wait, then it could wait. Dean then reached ito his backpack for some paper to take notes on the play he didn't read, and swore under his breath when he realized he forgot to pack paper of all things for the first day of school. He leaned over to ask Kevin for some when he noticed that Kevin was absent.

_What the hell?, _Dean thought. _Where did Kev go? He was just there…_

Dean leaned over and tapped Castiel on the shoulder and, after Cas gave him a puzzled look, Dean pointed to Kevin's empty seat.

Castiel looked just as puzzled as Dean. Dean raised his hand.

"Yes Mr…?", said Ms. Carr.

"Winchester, Ma'm. May I please use the restroom?", Dean asked suavely.

"I'll allow it since you asked so politely, but in the future let's go before class starts, okay Mr. Winchester?", Ms. Carr said so ever-so-politely. Not even the teachers could totally resist the charm of "Dean motherfucking Winchester".

"Thanks Ma'm," Dean said just as smoothly and, making a mental note to get class notes form Cas later so he wouldn't bomb the inevitable test over this, left to find Kevin.

Dean looked into every room in which there was not a class in session. All of the ones that he checked were empty, and just as he was about to check the last one at the end of the hall, he noticed shadows from the door crack and voices coming from the inside of the classroom.

Ready to barge into the classroom, Dean came to a halt when he heard _who _it was talking behind that door.

_Ruby! _Dean growled in his head.

He put his ear up to the door and listened.

"…So yeah, I've totally got little Sammy wrapped around my pinky finger. He doesn't suspect a thing.", Ruby said in a most bitchy voice.

"Yeah," laughed Ash, "he totally ate up your whole church camp alibi."

"Which was true," smirked Ruby, "if you count the occult as a church," she added cackling.

_I knew it!, _Dean said to himself, _I knew that harlot and that traitor were fucking!_

He had to stop and think for a minute about what they just said before it hit him. Did Ruby just say that she was at a satanic slumber party? Dean kept listening.

"Speaking of which, When is the next bonfire orgy? I'm fucking horny here," said a female voice unfamiliar to Dean.

"I can take care of you, Ivy," teased a cocky British voice Dean immediately recognized as Crowley, "you don't mind sharing, do you Meg?", he teased.

"It doesn't matter, we broke up!", Meg Masters mockingly cracked up.

"Don't even get me started on Gossip Girl," said the girl called Ivy, as she stripped down bare-ass naked (a sound to which Dean Winchester was so familiar that he could recognize it through a door. "humans are so fucking stupid."

Through the door, Dean could hear Crowley mount Ivy and start pounding away at her. Dean didn't know whether to run away, throw up, or faint. Satanic cults? Orgies? Fucking in the classroom with other people around? Dean knew that it wasn't a good idea for him to stay for risk of getting caught, but something kept him rooted to where he was sitting, almost as if a divine force was calling him to do so.

"You're dating that nerd Castiel now, right?," Ruby asked Meg as the moans from Ivy and Crowley got grotesquely loud.

"Only for appearances," Meg said. "Think he would make a good meat-suit."

"Unless he's already taken," said Crowley between waves of sick pleasure.

"What are you talking about, needle-dick?," Ash taunted as Ivy pushed Crowley off of her out of boredom.

"I'm saying," Crowley began, not seeming distraught by his inability to please Ivy, "that maybe he is not human."

"I think you might be right," said Ruby, "the power I feel emanating from him is arousing both physically and sexually," she added with a smirk.

"Hey watch out bitch, that's my boyfriend you're talking about," said Meg jokingly.

"Whatever. Anybody know who would make a good meat suit for Abaddon?", Ruby asked.

"How about Channing?", asked Ivy, "I have like three classes with the bitch and she's capable of processing loads of information [a trait of liable demon vessels]. I think she would be a good candidate."

"Yeah okay, we'll take the shifter's word for it," Ash mocked.

"Watch it asshat," Ivy warned.

"Ivy's right," said Crowley, "Channing is a good meat-suit, especially for someone of Abaddon's… ferocity."

"Alright then, it's settled. We'll lure Channing into a trap for Abaddon. Back to class Lucifer's Angels."

Dean's survival instincts kicked in. He ran (silently) to the nearby janitorial closet and left the door open a crack. So much information he had processed in such a little amount of time. Meatsuits? Abaddon? Lucifer's Angels? Castiel _not human_? That last one stuck with Dean especially.

He waited for "Lucifer's angels" to come out of the classroom, but to his horror, the only person that came out of the room was the girl that must have been Ivy, an adorable, short, strawberry-blonde-haired girl who looked no older than fifteen. None of the others came out of the room, and as Ivy walked away, Dean swore he heard her mutter under her breath, "I wish I could teleport."

Dean was terrified, and that was not usual for him. He was, after all, Dean motherfucking Winchester. But would you not have been scared in that situation? He stayed in the closet for the rest of first period, waiting for the bell to ring so he would no it was safe to leave.

He still could hardly accept what he had just overheard, but he knew that he had to tell people about it. So _many _people. Where to start? This matter concerned so many people Dean cared about. Castiel, because Meg (about which Dean wasn't completely positive was true), Sam, because Ruby, and Kevin because Channing.

The only thing Dean knew for certain was that he would never leave Ruby alone with his baby brother for one second. Not after what he just heard. He decided it would be wiser to keep a watchful eye than to tell Sam since he wouldn't believe Dean because God bless that boy he only looked for the good in people.

The bell rang and Dean left the closet, deciding to go to Cas since Cas was his best friend and would believe anything Dean said, because he trusted him. As Dean turned around a corner, he saw something that made his heart stop. Castiel, his best friend, was making out with Meg Masters in front of his locker.

Dean ran to the courtyard and just barely caught Sam before he went to his next class. He grabbed him by the arm and started dragging him in the direction of the impala.

"What are you doing Dean?!", Sam asked angrily.

"I'm sick," Dean ad-libbed, "I spent all of first period hurling. I think it's a virus and I'm worried that you might be a carrier. I don't want it to spread."

Dean kept dragging Sam despite all of Sam's protests, hell-bent on getting back to the safety of his Brooklyn loft before he had a heart attack.


End file.
